CAS 1258-84-0|Pristimerin

Introduction：Basic information about CAS 1258-84-0|Pristimerin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Pristimerin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles19
7. Synonyms

Common Name	Pristimerin
CAS Number	1258-84-0	Molecular Weight	464.636
Density	1.2±0.1 g/cm3	Boiling Point	607.7±55.0 °C at 760 mmHg
Molecular Formula	C₃₀H₄₀O₄	Melting Point	219.5°C
MSDS	ChineseUSA	Flash Point	195.1±25.0 °C

Names

Name	Pristimerin
Synonym	More Synonyms

Pristimerin BiologicalActivity

Description	Pristimerin is a potent and reversible monoacylglycerol lipase (MGL) inhibitor with an IC50 of 93 nM.
Related Catalog	Signaling Pathways >>Anti-infection >>BacterialNatural Products >>Terpenoids and GlycosidesResearch Areas >>Cancer
Target	IC50: 93 nM (MGL)[1]
In Vitro	Pristimerin inhibits the activity of purified MGL with an IC50 of 93±8 nM and that of non-purified MGL (cell lysates of MGL-transfected HeLa cells) with an IC50 of 398±68 nM. Pristimerin inhibits MGL through a mechanism that is rapid, reversible and non-competitive. The binding of pristimerin to MGL might be strengthened by formation of a polar interaction with a regulatory cysteine, possibly Cys208[1]. Pristimerin inhibits HFLS-RA and HUVEC cell viability in a dose- and time-dependent manner. Pristimerin decreases VEGF-induced autophosphorylation of VEGFR2 and attenuates the activation of the VEGF-induced VEGFR2-mediated signaling pathway [2].
In Vivo	Pristimerin inhibits inflammation and tumor angiogenesis. Pristimerin significantly reduces vessel density in synovial membrane tissues of inflamed joints and reduces the expression of pro-angiogenic factors in sera, including TNF-α, Ang-1, and MMP-9[2].
Cell Assay	HFLS-RA (5 × 103 cells/mL) or HUVECs (1 × 104 cells/well) are seeded in 96-well plates and cultured in normal growth medium for 24 h. The cells are then incubated with different Pristimerin concentrations (0, 0.125, 0.25, 0.5 μM). The effects of Pristimerin on HUVECs viability are determined under VEGF-induced conditions. Cell viability is quantified by MTT assay. At 4 h before the end of the culture period, 30 μL of MTT solution (5.0 mg/mL) is added to each well. Cells without Pristimerin or VEGF served as a vehicle control[2].
Animal Admin	Rat: Pristimerin is dissolved in DMSO (0.4%) and intraperitoneally injected daily into Male Sprague-Dawley rats in the experimental group (low-dose group, 0.40 mg/kg of body weight; high-dose group, 0.80 mg/kg of body weight) from day 11 to day 24 of immunization. The model group received vehicle (DMSO, 0.4%), and the normal control group received normal saline (NS). Methotrexate (positive control) is suspended in NS and orally administered in the autoimmune phase at an interval of 5 days[2].
References	[1]. King AR, et al. Discovery of potent and reversible monoacylglycerol lipase inhibitors. Chem Biol. 2009 Oct 30;16(10):1045-52. [2]. Deng Q, et al. Pristimerin inhibits angiogenesis in adjuvant-induced arthritic rats by suppressing VEGFR2 signaling pathways. Int Immunopharmacol. 2015 Dec;29(2):302-13.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	607.7±55.0 °C at 760 mmHg
Melting Point	219.5°C
Molecular Formula	C₃₀H₄₀O₄
Molecular Weight	464.636
Flash Point	195.1±25.0 °C
Exact Mass	464.292664
PSA	63.60000
LogP	7.54
Appearance of Characters	orange
Vapour Pressure	0.0±3.9 mmHg at 25°C
Index of Refraction	1.582
InChIKey	JFACETXYABVHFD-WXPPGMDDSA-N
SMILES	COC(=O)C1(C)CCC2(C)CCC3(C)C4=CC=C5C(=CC(=O)C(O)=C5C)C4(C)CCC3(C)C2C1
Storage condition	Store at -20°C
Water Solubility	DMSO: ≥5mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC4905000

CAS REGISTRY NUMBER :: 1258-84-0

LAST UPDATED :: 199309

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C30-H40-O4

MOLECULAR WEIGHT :: 464.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(1),90,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(1),90,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(1),90,1982

Safety Information

RIDADR	NONH for all modes of transport

Articles19

Pristimerin, a naturally occurring triterpenoid, protects against autoimmune arthritis by modulating the cellular and soluble immune mediators of inflammation and tissue damage.

Clin. Immunol. 155(2) , 220-30, (2014)

Rheumatoid arthritis (RA) is a chronic autoimmune disorder affecting the synovial joints. The currently available drugs for RA are effective only in a proportion of patients and their prolonged use is...

Targeting tumor proteasome with traditional Chinese medicine.

Curr. Drug Discov. Technol. 7(1) , 46-53, (2010)

The proteasome is a multicatalytic protease complex whose activity is required for the growth of normal or tumor cells. It has been shown that human cancer cells are more sensitive to proteasome inhib...

Biomimetic synthesis of xuxuarines Ealpha and Ebeta: structure revision of Rzedowskia bistriterpenoids.

Bioorg. Med. Chem. 16(4) , 1884-9, (2008)

Reaction of pristimerin with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a biomimetic-type coupling leading to xuxuarines Ealpha and Ebeta and not the previously reported Rzedowskia bi...

Synonyms

Methyl (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-2-picenecarboxylate

Methyl (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate

Methyl (2R,4aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-2-picenecarboxylate

2-Picenecarboxylic acid, 1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-, methyl ester, (2R,4aS,12bR,14aS,14bR)-

2-Picenecarboxylic acid, 1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-, methyl ester, (2R,4aS,6aS,12bR,14aS,14bR)-

Celastrol-methylether

pristimerine

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